@Ken Kast  Focus on the viability of STR's in Northern Grays Ferry not STR's in Philadelphia more generally.

That means I can ask my insurance to pay me the higher Actual Cash Value instead of the Dwelling A Coverage?   

If you don’t have HOA or pay any of the Utilities. …..now the problem is in the Tulsa area that deal that rents for $2000+ mo and can be purchased “all in” for $150K is much harder to find. 

We have a lot of equity in the properties under the loan.

As other mentioned it's ultimately on the business owner to track income/expenses. 1099s being issued are more a compliance piece on their end to ensure you're reporting income. 

I manage tons of homes for investors and owners, and I have this conversation all the time.

What are you estimating the value, $450k? 

Quote from @Brad Tooley: Hello, I' m looking to start a career in real estate investing and want to find a job that will teach me a lot about the industry while also paying well so I can start saving for down payments and all the expenses that come with my investments.

The one I’ve spoken to says 25% down and I’m looking for lower than that.Hi Abby, I have the best lenders in the game and they have special loan programs that let you do way less than the normal 20% down.

This basis would be divided between the two houses.